crossdressingstories
patreon
The Raise
🕑 Added 2022-11-20 21:31:14 +0000 UTCFirst let me set the stage, I am a lifelong cross dresser, since I was 13 and trying on Mom’s things when she was out. I am NOT gay, nor bi-curious, I am heterosexual and this is my story.
My wife travels a great deal in her job, I am lucky and stay home, we have no kids even though we have been married 10 years. I went through 8 years of secretive panty wearing and dressing up and all that changed when she came home a day early. I am 5’ 6” and when fully painted and dressed can pass as female in a lot of the bars around here. I know because I would sneak out dressed late at night to see if I could.
My wife had gone away for what was supposed to be a 10-day visit to a subsidiary. So as usual as soon as she left I dug out my secret trunk and dressed up every day after work. I would put on my padded bra (36c) tight cock hiding panties, hose and garter, and black mini skirt with a sheer top. God just looking at myself I always got horny and always waited for hours before bed to relieve it. In bed I would take my wife’s nighties and wear them always carefully washing them before her return.
It was Saturday night and Julia (my wife) was not due home until Tuesday so I was reveling in my female attire watching TV. I was dressed in a sexy tight black sweater, my bra, mid thigh skirt with a slit to my hip, thigh high hose, 3 inch heels (black of course) and had my wig in full splendor. I had painted my toes and fingers a deep red and matching lipstick with a dark eye shadow and foundation. I looked and felt every inch a woman, though I laughed a lesbian one.
Suddenly the door opened and there stood Julia, I froze unable to think or respond. I just stared at her, she was in her business suit, but minus the blouse, which revealed her ample cleavage and her skirt was just above her knees. She looked like a drop dead gorgeous lady and at 34 and 5’ 4”she was. Long red hair flowing past her shoulders, slim legs, thin waist, great ass.
“Well I came home to surprise you and it seems you surprised me!” Exclaimed Julia.
“I, uh, guess so Hun, I don’t really know what to say.” I stammered out.
“Say? Say nothing, stand up and let me look at you.”
Doing as requested I stood and turned slowly for her, she came over and touched me and fondled me a bit and generally admired me. There was no trace of anger or resentment and for this I was grateful.
“So sweety, what name do you go by while I am away on business?”
“J-Jennifer.”
“It’s ok Jennifer, I am not mad at all, in fact, I find it stimulating.”
Then Julia did the totally unexpected, she kissed me and not her usual kiss. It was softer, more sweet and lingering. Her hands caressed me, not held me, and she let them wander all over my back. I found my own kiss was softer and less aggressive than as John, and her heat felt better than ever.
We found ourselves getting very hot and she invited, no grabbed me, and headed upstairs. In out bedroom she removed her jacket and skirt and lay me on the bed. She continued her kisses and caresses slowly exposing my skin to her touch. She was really getting into when she stopped.
“What’s wrong?” I asked.
“Well Jennifer you look great and all but…”
“But?”
“Too hairy, come lets go to the bathroom.”
Meekly I followed both intrigued and nervous. Once there she got out the scissors and razor, now I was nervous. She just smiled and told me to relax and sit on the tub edge. First she trimmed my underarms and carefully took her electric razor and shaved them smooth. Then she tackled my legs, I am not naturally hairy so that went easily enough. Then carefully pushing my thong aside she trimmed the edges of my pubes. She stood back and smiled.
“There, look for yourself Jennifer.”
I stood and looked in the mirror and liked what I saw. It wasn’t John anymore it was Jennifer. She turned me and kissed me again leading me back to the bed. There we now really started going wild, me stripping her and kissing her nipples, slowly and tenderly invoking moans from her as I did. My fingers found the waistband of her panties and slid them off her. I went to her mound and using just my tongue I traced her lips to her asshole then back up to her clit. I opened the hood with my tongue and circled her clit slow and long invoking more moans and whimpers. My own thing panties were stretched tight and felt wonderful, as I was still Jennifer, a woman making love to her woman.
Her orgasm rolled up slowly and suddenly she was grabbing my head and grinding her pussy into me. I was driving my tongue deep into her with each thrust until she collapsed and lay there panting. I moved up beside her and kissed her, letting her taste herself on my lips.
“My darling Jennifer, that was superb, now it my turn to eat you.” She smiled.
Eat me? I wondered? Then I had my answer. She lay me on my tummy and pulled off my thong and had me pull my very erect cock under my tummy. She then split my ass cheeks and began to tongue me there. It was heaven, divine pleasure as I felt her tongue work past my sphincter muscle and work deep inside me. Each thrust and roll of her tongue was driving me insane with pleasure. It took only a few minutes for her to make me orgasm spilling my cum onto the sheets under me.
The she turned me over and slid my panties down and sucked my cock until it was hard again. Once hard she slid her furry pussy over the head of my cock and rode me. She rocked back and forth as she fucked Jennifer, me, for several minutes. As I felt her pussy walls begin to shudder and squeeze I had my own orgasm inside her. She collapsed on top of me resting there as my cum dribbled out of her onto me.
“Oh Jennifer, I have always wanted you, I just never knew how to tell you. I knew you dressed up and longed to have you as my woman husband.”
I was dumbfounded, was this real??
“I really came home early to tell you that my subsidiary has offered me an upper management in that city. If we can leave John behind and go as Jennifer and Julia I want to accept.”
“YES!” Was all I said as we drifted off to sleep, happy that my dream was about to come true.
